Sissy Doctor Stories

36,636 results
Orientation
Length
Source
Infinite Scroll

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

In Need of Counselling

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

I knew my wife, Becky was unhappy just before Christmas. We had been married for five years and she seemed dissatisfied with everything. We had been incredibly unlucky. I'd been made redundant, we seemed incapable of having children and I had lost interest in sex. I refused to accept that there was anything wrong with our relationship yet she insisted we saw...

Becoming the Sissy Slut

by HappyCouple74 on Oct 6, 2020
Transgender & Crossdressers

Story 5 "You are going to have to go, I don't see a choice here." My boss said to me. I didn't want to go on this trip. It was a routine check of one of our automated sites. That meant about 10 days of living in a hotel and checking in to the control room once a day just to see how the automated diagnostics were going. Normally, we send Gary, the junior st...

A Game within a Game Ch. 02D

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2D. Another session - or not. The next morning...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

Letter from a Colleague Pt. 01

by 1Gratiano on Jul 15, 2020
Transgender & Crossdressers

Dearest Doctor Gratiano, I had been enjoying your communications immensely, and had often wondered how I might actively profit by your insights, when a quick peek at my husband's browser history made it immediately clear that he could be made into the perfect obedient husband — or perhaps I should say wife? Things really began to develop after he was laid...

Doctors Orders 1st Appointment

by Misslexia on Sep 13, 2017
Fetish

It was one of those days when things kept went wrong, right from the start. My alarm didn't go off, so I dressed hastily. I missed my train; I left my lunch at home and so on. It wasn't until I was almost too late that I remembered that I had a doctor's appointment that evening. I ended up having to run to catch my train, which was not a good idea as my appo...

The Visitor Ch. 09

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

This is the continuation of the story of my foolish submission to an online Master, who actually became my visitor and all the things that happened as a result. It describes how I slid further and further under his control, by his use of drugs, heavy persuasion and as he is a doctor, the changes he made to my body to prevent my escape from him. This particu...

Kimmy's Discovery Ch. 05-06

by Deviana on Dec 17, 2018
Transgender & Crossdressers

Sensations I had never experienced or even imagined continued to flow throughout my body. Lola's hand was warm, soft but firm, as she guided me to remain between her and Karen. The line to the ladies' room finally dwindled and we were next. And as one of the stalls became available, Lola and Karen pressed me in with them. My body pressed close to them, I sto...